


A Betting Man

by allmylovesatonce



Category: Brooklyn Nine-Nine (TV)
Genre: Gen
Language: English
Status: Completed
Published: 2016-08-23
Updated: 2016-09-30
Packaged: 2018-08-10 13:37:55
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 14,915
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7847170
Author URL: https://archiveofourown.org/users/allmylovesatonce/pseuds/allmylovesatonce
Summary: <blockquote class="userstuff">
              <p>Set after Jake returns from Witness Protection:<br/>Jake wants to move forward in his relationship with Amy and takes unnecessarily complicated steps to do so.</p>
            </blockquote>





	1. The Setup

In hindsight, work might not have been the best place to decide to look at engagement rings. But Jake couldn’t help that he’d finished a case and had some time on his hands. He was thankful for his quick reflexes when Amy walked up behind him.

“What’s that?” Amy asked.

Jake quickly changed screens. “Nothing. Porn. I don’t know.” He looked up at Amy’s confused face.

She stared at him for a second before responding. “I was just asking out of curiosity. I wasn’t interrogating you.”

“Yeah, well here,” Jake replied, gesturing to the precinct, “We’re just partners. So you don’t get to know what’s in my browser history, Detective Santiago.”

Amy looked at him with a bemused expression.  “I was just being friendly as I walked by, but now I’m genuinely wondering what it is you’re looking at, Jake.”

Jake scrambled to close out of the rings page on his computer before Amy could come back around his side of the desk. She leaned over his shoulder and looked at the screen but it was just his desktop. He looked up at her and shrugged. “Like I said, nothing to see here, Detective.”

She squinted at him. “You’re being weird.”  She turned and walked back to her desk.

“You’re being weird,” Jake parroted. She shook her head at him and got back to work. He leaned his head on the back of his chair and sighed, relieved to not have been truly caught. He decided then and there he needed to be more careful.

~~

Before Witness Protection, Jake thought he and Amy were moving at a comfortable pace. He loved her and was all about moving in with her until Jimmy Figgis messed it all up. Spending three months away from Amy was utter hell. From the moment he saw her as she ran into his arms, he knew he wanted more. He never wanted to be away from her again. He wanted to live with her, but more than that, he wanted to marry her.

The problem with his realization though was that getting back into the routine of things was hard. They didn’t bring up living together right away. He just basically spent all his nights at her apartment. They were both so happy to just be with each other again that big life decisions got pushed aside. But almost every night he thought about it. He’d look over at her gorgeous, peaceful face as she slept and think of spending the rest of his life with her.

The problem with being in a mature, adult relationship though, was that Jake felt like he had to mature with it. And though he felt he’d come a long way even since he started dating Amy, he didn’t feel like it was enough. The longer he stared at her as she slept, the more afraid he got of letting her down.  She was so much better than he was and he was worried that if they actually lived together and got married that he and his crushing debt would bring her down. So he never mentioned his intentions to marry her. He never brought up their conversation from before he left about living together. And neither did she.

~~

Amy couldn’t begin to explain the joy and the relief she felt having Jake back in Brooklyn. It had been two months and each day had been wonderful. Sure, there were some days where work was rough and her leads didn’t pan out. But then she’d look up and see Jake sitting across from her. It didn’t matter what he was doing. He could be absorbed in a case of his own or messing around with Boyle. Either way, she felt happier just seeing him there again.

She didn’t think she’d been happier than the months that he’d been back from Florida. But underneath all the happiness, something was eating at her. They’d made a pretty big decision right before he left. Then he spent three months away from her. Maybe it was silly of her to think that they’d put their cohabitating plans into action right when he got back. He’d never even mentioned it. She figured he had a lot on his mind so she didn’t mention it either. But every night he would stay at her apartment and she would wonder as he slept.

Amy was not the type to be spineless. She wanted to know what was going on in their relationship. But Jake had just gotten back from Witness Protection. It had to be hard for him. So she held her tongue until she thought it was a better time. Before she knew it, two months had passed and they still hadn’t talked. She was losing her ability to keep quiet when Jake started acting strangely.

~~

Jake stood up from his desk and walked to the evidence lock up. He was filing something when Amy walked in. Looking up, he smiled at her, almost derailing the reason she followed him. She needed to know what was happening. She needed to know why she had a bad feeling in the pit of her stomach. And Jake was the only person who could give her those answers.

“Hey, what’s up?” He asked, still smiling.

“I don’t know, Jake. What _is_ up?” Amy replied sharply.

Jake looked taken aback. “What’s going on?”

Amy shrugged. “I’ve been asking myself the same question for a while.”

“Ames, you’re gonna have to be a bit less vague. I really have no idea what you’re talking about here.”

Amy walked closer to Jake. She sighed. Now that her moment had actually come, she was nervous. What if everything was fine and she was just paranoid? What if interrogating Jake would create a problem where there wasn’t one? Jake looked at her questioningly. She took a deep breath and started speaking. “I thought we had plans, Jake. I thought when you came back we’d act on those plans. But now it just feels like our relationship is stuck in some holding pattern.”

“What?” Jake asked like she’d said something truly absurd.

“Oh come on, don’t deny it. We aren’t moving forward at all,” Amy pressed.

Jake flashed her a bewildered look. “Amy, it’s only been two months.”

Amy shook her head. “Yeah, but it’s been two months of nothing,” she insisted.

Jake took a step back, the wind taken out of his sails. “Wow. And here I thought it had been pretty nice. I was just happy to be back.”

Amy realized her mistake immediately. She stepped towards him. “Jake, that’s not what I meant.” Jake continued to retreat. “I just imagined things would be different once you got back.”

Jake stood silent for a beat, clearly contemplating what to say next. Before he could speak, Charles walked into the room. Both Amy and Jake snapped their heads in his direction.

He looked startled. “Whoa. Am I interrupting something?” he asked nervously.

Amy nodded. “Yeah, kind of.”

“What is it, Boyle?” Jake asked. Amy turned back to look at him. He looked hurt. She hated herself for doing that to him.

“Uh, Sarge wanted to see you, Jake. But I’m sure it can wait till you’re done here,” Charles replied.

Jake’s eyes flickered over to Amy before looking back at Charles. “That’s okay. I don’t want to keep him waiting,” Jake said, moving towards the door.

Amy stepped towards Jake in his path to the door. “Jake,” she started.

Jake looked up at her, the hurt still clearly written across his face. “We can, uh, talk later. Okay?”

Amy made a small whining noise, not wanting to leave their conversation like this. Regardless, she nodded and let him go.

She waited all day for the chance to talk to Jake again but the chance never arose. Jake was still working when she got roped into going to Shaw’s with the rest of the gang.

~~

Jake was working on an assignment for Terry when everyone left. He’d been relieved when they all left. He’d had a knot in his stomach ever since his talk with Amy earlier. He could feel her eyes on him the rest of the day. He still didn’t know how to fully explain to her what he was feeling. It was just easier not to try. That is until she cornered him and said their relationship was going nowhere. It had been a blow he didn’t see coming and one he’d felt the rest of the day.

It wasn’t long after everyone had cleared out that Terry walked over and sat in the chair next to Jake’s desk. Jake looked at him questioningly. Terry sighed before he spoke. “Okay, what’s going on?”

Jake feigned ignorance. “What do you mean, Sarge?”

Terry scoffed at him. “Please, you’ve been off all day. What’s going on?”

“I don’t know what you mean,” Jake lied.

Terry stared at him with a knowing look. “Jake, I’ve known you for a long time. Something’s wrong. Why don’t you just tell me about it?”

Jake sat further back in his chair and looked around the precinct. It was mainly cleared out. He spoke quietly, still not wanting to really talk about it. “Amy and I had a fight.”

“What? You guys never fight.”

Jake nodded. “I know. But she cornered me earlier and wanted to know why our relationship wasn’t going anywhere.”

Terry looked confused. “I wouldn’t have thought that your relationship was going nowhere. You guys are great together.”

“Yeah, well apparently since I’ve been back, Amy hasn’t thought so,” Jake responded.

Terry spoke hesitantly. “Is there…maybe a reason she thinks that?”

Jake rubbed a hand over his face. “Yeah, there might be.” He looked over to see Terry giving him a sympathetic look. Jake looked around again before leaning in closer to the sergeant. “Can you keep a secret?”

Terry nodded enthusiastically. “Terry’s great at keeping secrets.”

Jake pointed at him. “And if this comes up in conversation with someone else, you have to play dumb. No one can know about this, okay?”

Terry nodded excitedly, leaning in closer to Jake.

“I’ve been…looking at rings,” Jake basically whispered.

“Oh my God. Really?” Terry asked eagerly.

“Yeah.”

“So then why does Amy think your relationship is going nowhere?”

Jake sighed. “Because she doesn’t know.”

Terry stared at him. “She doesn’t know you want to marry her?”

Jake shook his head. “Nope. I kinda realized how badly I wanted to when I got back but then I started looking into rings and, I don’t know if you know this Terry, but engagement rings are expensive.” Terry laughed. “So I didn’t mention it, because thinking about spending that kind of money made me think about how financially challenged I am.”

“That’s one way to phrase it,” Terry replied.

Jake glared at him. “I want to move in with her. I want to marry her. I want to move forward in our relationship sooner rather than later. I just don’t want to drag her down with my debt. She’s so great about money and all that junk. I don’t want her to be stressed out trying to fix my own stupid mess.”

Terry stared at Jake disbelievingly. “Wow.”

“Are you thinking I sound stupid?” Jake asked nervously.

“No, I was thinking you sounded like an adult. Which no offense, Jake, isn’t always very common for you.”

“Hey, offense taken!” Jake exclaimed.

Terry ignored him and continued talking, “Look, Jake, your reasons are completely valid. They’re good reasons for being hesitant. Why don’t you just tell Amy this?”

Jake’s expression turned sour. “You know I don’t like to talk about these things, Terry.”

Terry shook his head at him. “Sorry, Peralta, but that’s part of being in an adult relationship.” He reached out and grabbed Jake’s shoulder. “I’ve seen you handle these things before. Why don’t you just tell the woman you love, who loves you back, why you’ve been acting so weird?”

Jake groaned. “Ugh, I guess I can do that.”

“Good. And then get engaged so I can be publicly happy for you. Because it’s gonna be hard to keep this a secret.”

Jake pointed at him, “Hey! You said you’d keep it a secret!”

“I will,” Terry promised. “Now why don’t you go find Amy?”

Jake motioned to his desk, “I still have this thing I was working on for you.”

“Eh, it’ll still be there in the morning. Go find your lady!” Terry replied excitedly.

“I’m not proposing tonight,” Jake clarified.

“Just go!” Terry shouted.

~~

Amy had been at the bar for a few hours. She was with her friends so she should be having a good time. But she couldn’t stop beating herself up about the fight. She and Jake never fought. And yet she just had to corner him and make him talk about things. And at work, no less. What had she been thinking? She didn’t want to fight with Jake. She just wanted to know why things felt off. Apparently they didn’t to him. The image of his hurt expression wouldn’t wipe from her mind. She just kept replaying the way he stepped away from her. She’d been an idiot.

She wasn’t listening to a thing that her friends had been saying. They could have been speaking in a foreign language for all she’d understood. Boyle was talking about some weird restaurant and Gina was talking about herself, as per usual for both of them. It wasn’t until she felt a nudge against her shoulder that she was pulled out of her own thoughts. She looked over at Rosa.

“What’s up with you?” she deadpanned.

Amy shook her head and shrugged. “Nothing. I’m fine. I think I’m just a bit spacey.”

“You’ve had more than one drink. You’re not spacey,” Rosa replied.  Amy rolled her eyes, wishing her coworkers had not catalogued her reactions when drinking.

“I’m just having a weird day,” Amy answered.

Rosa laughed to herself, “Yeah, Jake working longer than you, that’s a weird day for all of us.”  Amy grimaced at the mention of Jake, still feeling bad. And just like that, it all dawned on Rosa. “Oh.” There was a long pause between the two of them. Rosa took a long pull of her beer before turning back to Amy. She looked pained when she asked, “Do you want to talk about it?”

Amy half smiled at Rosa’s efforts, shaking her head. “I’m okay.” She looked over at the bar. “But I am going to get the next round.” Amy looked back at the table before she walked to the bar. Between the four of them, they’d already had entirely too much to drink. The other three had consumed way more than she had and she’d had four beers. Maybe another round was a bad idea. She still stalked over to the bar interested in another round for herself.

She was waiting on her beer when she heard her name.

“Amy?”

She looked to her right and it was none other than her ex-boyfriend Teddy. Timing was weird. But that always seemed to be the case for Amy’s life.

“Teddy?” She replied. “Wow, what are you doing here?”

He gestured over to a table on the other side of the bar. “I’m here with some buddies.”

She gestured to her friends. “Yeah, same.” Her beer came and she grabbed it, ready to head back to her table.

“So how’ve you been?” Teddy asked, keeping Amy at the bar.

Amy’s never been the type to want to “win the breakup” but she also didn’t feel like divulging how crappy her day was to her ex. So she plastered on a fake smile. “I’ve been pretty good. Yeah, work is great,” she said, hopefully convincingly.

He nodded approvingly. “I heard it’s been pretty crazy at the Nine-Nine.”

“Oh?” Amy was curious what he’d heard. She sat down in one of the chairs.

“Yeah, I heard some mob boss put a hit out on the Captain and one of the detectives and they had to go into witness protection. Is that true?” Teddy asked, staring her down.

Amy nodded solemnly. “Yeah. Holt and Peralta were gone for months,” she confirmed. She used Jake’s last name in hopes that Teddy wouldn’t ask any questions about him.

“That’s crazy.”

“Yeah. Although, it did lead us to one of the best stings we’ve probably ever had. Getting to take down a major mob boss is a fun line to have on the old résumé,” Amy hyped.

Teddy looked impressed. “That sounds intense.”

Amy nodded, smirking. “It really was.”

“And the Nine-Nine pulled that off? Not the FBI?” Teddy asked.

He couldn’t have known he’d get the full story. Or maybe he did. Either way, Amy was pouring back her fifth beer and her confidence was setting in. She leaned forward in full story telling mode. She started probably farther back than she should of. But he learned all about Adrian Pimento and how she, Amy Santiago, did time at the women’s prison to get information out of Figgis’s sister. He learned how they took down Figgis’s operation which led him to put a hit out on Holt and Jake, leading them to Florida. He got the full story of the hard work that went into the operation that ultimately took down Jimmy Figgis. She got more animated and was more excited telling Teddy that story than she was for easily the last three months of their relationship.

~~

Jake walked into Shaw’s and quickly found his friends’ booth. They all seemed plastered. It didn’t seem fair that they were all trashed and he’d been working late. That was never how it happened. He looked at the three pitchers on the table and grinned.

“Hey guys, having fun?”

“Jake!” The three of them yelled in unison.

Jake laughed. “And how much have we had to drink?”

Gina gestured to the pitchers in front of them. “We had one each!” She clarified.

Jake gaped at them. “My God. You realize you have to work tomorrow, right?” It felt weird that he seemed like the adult in this situation. It was happening more and more and he didn’t like it.

Gina sat up straight and grabbed the table. “Wait! It’s not Friday?” Jake just shook his head. “Oh my God, I’m gonna have to call in sick tomorrow. None of you saw me here,” she said, sliding down in the booth trying to hide behind the table.

“Wow,” Jake muttered to himself. “Hey, I thought Amy was with you guys.”

Boyle picked his head up off the table, answering, “She went to get herself another drink. It’s been a while. I think. I’m losing the concept of time.” Jake shook his head humoredly. Before he could step away from the table, Boyle grabbed his arm. “We’re still best friends, right, Jake?”

Jake chuckled at how drunk Boyle was. He patted him on the head and said, “Yes, Charles, we’re still best friends. In fact we’re such great friends that I’m going to call Genevieve to come pick you up.” Jake could hear Boyle’s sigh of relief at his reply.

Jake was still chuckling when he turned to the bar and spotted Amy. She was talking pretty animatedly to someone. He swore he recognized the back of that guy’s head but he didn’t know why. Had he arrested the guy? The man turned to face the bar and Jake realized who it was. Amy’s ex. Perfect.

~~

“And then we put Figgis away. And we, the Nine-Nine,” Amy paused, faking a sniffle, “we brought our boys home.”

Teddy looked enthralled. “Damn, that’s crazy. You guys pulled of a pretty big sting for just being NYPD.”

“ _Just_ NYPD? You insult your own badge, Sir,” Amy answered. “We learned a long time ago that we could basically take down any of the other windbreakers. It’s fine. I guess the Nine-Nine is just the top,” Amy continued, puffing her chest out.

The bartender placed another beer in front of Amy. She stared at it questioningly. “I didn’t order that,” Amy explained.

The bartender looked back up at her. “Yeah, it’s from the man over there,” she said pointing toward the door. Amy looked over quickly to see Jake exiting the bar.

“Crap!” She stood up suddenly, wanting to chase after him.

Teddy stopped her quickly. “Listen Amy, it’s been fun to catch up. Or rather listen to your stories. Would you want to get dinner some time? Maybe catch up for real?”

Amy sighed. “I’m sorry, Teddy, but I’m with someone. And he just saw me with you and he’s probably annoyed or worse. I really should go.”

“Oh,” Teddy started, taking it in, “you’re with someone?”

Amy took a deep breath before answering truthfully. “Yeah. Jake.” She saw a brief flicker of resentment cross Teddy’s face before it disappeared. “I’m sorry. But I should really go.”

Amy ran out of the bar, hoping she would find Jake still on the street. Unfortunately for Amy in her alcohol addled state, he was nowhere to be seen.

~~

Jake was sitting at his desk working when he heard the elevator ding. He didn’t even turn around when he heard his name.

“Jake!” Amy exclaimed, running from the elevator. She threw herself down in the chair next to his desk. He stayed focused on his computer. “Jake, will you please talk to me?” Amy pleaded.

He finished typing his sentence before looking over at her. “What’s up?” he asked nonchalantly.

Amy glared at him. “Don’t “What’s up” me. I know you saw me at the bar talking to Teddy before you left. I ran to your apartment and you weren’t there so I ran to mine and you weren’t there either. I stopped by Sal’s and you weren’t there. This was honestly the last place I expected to find you.”

Jake shrugged and looked back at his computer. “I had work to do.”

She grabbed his shoulder and turned his chair to make him look at her. “I’m sorry about what I said earlier. It’s not true and I –”

“You’re right, it’s not true,” Jake interrupted. He paused. “But I could see how from your perspective, it would look like we were standing still.”

“What?” Amy inquired.

Jake sighed. “You know I’m not great at expressing myself when I really need to,” he started.

“Yeah, I blame your dad,” Amy replied.

“Yeah, me too,” Jake said with a smirk. “Anyway, coming back was hard because I had all these steps I wanted to take in our relationship but I didn’t know how to do it. And then the more I started thinking about it, I realized it wasn’t fair to you to marry me and tie yourself to all my debt.”

Amy gasped softly. “Marry you?”

Jake looked up at her, not fully realizing what he’d said. “What? No. Gross,” he fumbled, looking away from her. She reached out and grabbed his hand. He looked back at her and saw the huge grin on her face. He covered her hand with his other hand. “Okay, yeah, I want to live with you and marry you, Amy Santiago. But I don’t want to drag you into my hole. I want to help provide for our life together not just mooch off you,” Jake explained. At her silence he added sassily, “So what do you think about that?”

She laughed. “I think it’s stupid that you won’t let me make my own choices.” He looked at her guiltily. She scooted closer to him and cupped her hands on his face. “Jake, I kinda knew what I was getting myself into when I fell in love with you.” He smiled broadly at her. “And I did it anyway.”

Jake leaned in and kissed her softly. She leaned her forehead against his, her hands still holding his face. “I love you, Jake Peralta. Crushing debt and all.” Jake laughed.

“I love you too, Amy Santiago.”

Amy pulled away and stood up. “You’re here far too late. You wanna head home?”

Jake stood up quickly and smiled. “Definitely.”  

Amy headed for the elevator and Jake couldn’t resist the thought that came to his mind.

“Hey Ames, I’ve got an important question for you.”

“Yeah?” She asked, turning around. She gasped at the sight of him down on one knee.

He very slowly reached forward to tie his shoe. “Sooo…your place or mine?” He asked with an impish grin.

She shook her head and turned away from him. She chuckled in spite of herself. “I hate you.”

He laughed loudly. “That’s not what you said two minutes ago!”

“So is this how it’s going to be until we actually get engaged?” Amy asked, exasperated.

Jake smiled as he wrapped an arm around her. “Most likely.”

“Well if that’s the case, I’m gonna say no.”

Jake looked at her knowingly and smirked. “No you won’t.”

~~


	2. The Bet

They were all gathered for the morning briefing when Jake was called up to discuss his new case. He had a B & E that went wrong and turned into a murder. The Captain had informed him that he needed to have someone be his secondary. Jake started discussing the important aspects of the case. He was about to announce the secondary he’d been assigned when he glanced at Amy and couldn’t resist messing with her again.

“Now, I have a very important, potentially life changing question for one member of this squad,” He said grandly, pausing to look at Amy. She looked back at him curiously. “Rosa Diaz,” Jake continued, looking away from Amy, “How would you like to be my secondary? Doesn’t matter if you say no, Captain already assigned you.”

Rosa nodded. “Yeah, sounds okay.”

Amy nodded too. “Yeah, and also, I hate you,” she said matter-of-factly.

Jake just smirked at her and walked back to his seat. He was oblivious to the stares directed at him by the rest of the squad.

It wasn’t five minutes after the Captain dismissed them that Jake was dragged into an interrogation room by Terry. Jake sat down in the perp’s chair and Terry stood over him. Jake wasn’t guilty of anything (that he knew of) but he was starting to sweat from the way Terry was staring at him.

“The way you posed your question to Rosa about being secondary – that was weird.”

Jake shrugged. “What? No it wasn’t. It was totally normal, Sarge,” he assured.

“No it wasn’t. It seemed like the start of a much more important question,” Terry insisted. He leaned in even closer to Jake. “It seemed like it could be…a proposal. So I have to ask, Jake Peralta, are you about to propose to Amy?”

Jake did his best to keep his expression flat. “That depends.”

“On?”

“On how many people are behind the glass,” Jake answered, pointing to the window.

“Fine,” Terry said, turning to the window. “Guys, come in here.”

Rosa, Charles, Gina, and Holt all walked single file into the room, joining Terry in standing over Jake.

“Really, Captain? _You’re_ even in on this?” Jake asked, astounded.

“I can’t help it. I was…curious,” Holt answered flatly.

Charles stepped closer to Jake. He was uncomfortably close. “Jake,” he started at a very low volume, “I need you to tell me _everything_.” By the end of his sentence he was much louder. Jake recoiled.

He stared at the five of them. “You realize Amy’s probably going to be suspicious of why none of us are at our desks.”

“Not to worry, Jakey, Hitchcock and Scully are distracting her,” Gina informed happily. Jake grimaced. He wouldn’t want to be on the end of that. “So, with that covered,” Gina continued, “Spill.”

Jake straightened in his seat. If he was going to be interrogated, he was going to act like almost every perp he brought in. “I don’t know what you’re talking about. I didn’t do anything,” he said in his best “perp voice.”

“Jake,” Rosa scolded impatiently.

Jake sighed. “Fine. But there’s really nothing to tell. Nothing’s even happened yet.”

“Wait. Yet?” Rosa asked.

“Yet? Did you say yet?” Charles interrogated, getting closer again.

“I think he _did_ say yet, Charles,” Gina replied.

“Elaborate on that for us, Peralta,” Holt ordered.

Jake blew out a long breath and looked at all of them. “So…I’m planning on proposing to Amy.” Charles and Terry cheered loudly. Gina immediately started explaining a proposal some celebrity did. Holt and Rosa nodded approvingly. Jake quieted the other three down. “Hey, she doesn’t know when or where, okay. Be cool.” They all stood still and listened to him. “ _I_ don’t actually know when or where yet.”

“Oh. My. God. Do you need us to help you?” Charles cried excitedly.

“Nope.” Jake thought about it for a second. “Well, maybe. I don’t know.” They huffed collectively. “Look guys, this is in very premature stages, okay. I don’t even have a ring. I also don’t know how to pay for a ring but that’s a problem for later.”

“Do you need help paying for a ring?” Rosa asked.

“Yeah, we’ll all chip in,” Charles insisted. Gina grimaced but then smiled and nodded. They all looked okay with the idea of helping Jake buy an engagement ring.

Jake shook his head. “No. This is probably the most important thing I’ll ever buy in my life. I need to do this myself.” He heard small gasps from his friends. They all looked slightly stunned. He was kind of offended. But then he realized how crazy it must seem that he was turning down a handout.

Terry was beaming at him. “You guys, I think it’s finally happening. Jake Peralta is growing up.” They cheered quietly.

“Hey, that’s rude,” Jake insisted.

“Is it rude if we’re proud of you?” Gina asked.

Jake thought on it. “Yep, still rude.” He stood up. “Well I’m gonna go get back to work. Rosa and I have that case to work on, so…” They were all staring at him with varying levels of happiness on their faces. Rosa and Holt were never expressive enough to make it look like true happiness. He edged away from them and toward the door. “Yep, I’m going. Bye,” he said awkwardly. He walked into the hall and closed the door behind him. Turning around he walked right into Amy.

“Whoa!”

“Sorry, Ames. Didn’t see you,” he explained.

She shook her head. “It’s fine.” She looked behind him toward the interrogation room. “What’s going on in there?” she asked, moving towards it.

He jumped in her way. “Nothing.”

She flashed him a disbelieving look. “You sure? Because no one is at their desks and I saw at least Sarge and Charles in there.”

Jake tried to act casual. “They were being weird. They wanted to know if I had any medicine for Rosa. She’s got some tummy troubles, if you know what I mean.”

“Hmm. Gotcha.”

“Yeah. Apparently nothing’s staying in long. It’s coming out of her like –”

Amy interrupted him. “Eww, Jake, I don’t need to know this.” She shook off the weird conversation. “So I have a surprise for you.” Jake nodded, encouraging her to continue. “I found us a place to live!”

Jake was confused. “What? I thought we already had a place to live. I thought I was moving into your place.”

“Yeah, we did say that,” Amy started. “But I didn’t want _your_ place or _my_ place. I wanted _our_ place. And I found it.”

Jake felt queasy. He didn’t want to deny Amy this when she seemed excited about it, but he already was worried about paying for a ring. He didn’t want her to set her heart on a place he couldn’t afford. “Ames,” he started.

“Don’t worry, I know how you’re feeling about money right now. I took that into account,” she insisted. His interest was piqued.

“If you say so. Show it to me,” Jake replied, aiming to get Amy far away from the interrogation room.

~~

Jake was helping his mom clean up after dinner. “So…where’s Dad?”

Karen glared at him. “He had a flight. He was sad to miss dinner though.”

Jake scoffed. “Yeah, I’m sure so. Amy _actually_ was sorry to miss dinner. She was still working on a case and she couldn’t leave,” he explained.

His mother smiled sweetly at him. “I know. You told me that earlier.” She looked over at him with her motherly knowing gaze. “You and Amy seem really happy,” she commented.

He smiled more to himself than to her. He nodded and looked up at her. “Yeah, we are. I mean we’re moving in together so I guess that’s a big step forward.” He paused, deciding how much he should tell his mom. “And also, I’m…thinking pretty seriously… about proposing to her.”

Karen dropped the plate she was washing in the sink. “Seriously?” Jake nodded. She shook her head in disbelief and walked over to hug her son. “Well when are you going to do it?”

Jake shrugged. “I don’t know. I need a ring to propose and that’s a pretty big obstacle for me right now.”

His mother touched his shoulder and looked sympathetic. “Oh, Jake, I –” suddenly she stopped talking and walked out of the room.

Jake was confused and after a second he followed her. He found her in her bedroom. When she heard him walk in she started explaining. “I think I temporarily forgot about this,” she clarified as she rifled through a jewelry box.  She pulled a ring out with a small “Aha.” Jake stared at it and then back at his mother. She held it up for him. “This is for you.”

He couldn’t hide his shocked expression. Suddenly he started questioning it. “Wait, this isn’t from Dad is it? Because I don’t want the ring of a failed marriage. No offense, Mom.”

She chuckled. “None taken. Also, it’s not from your father.”

Jake sighed in relief, taking the ring to inspect it. “I bet Dad didn’t even know you should propose with a ring. I bet he was just like, “Eh, let’s do this, I guess.” Right?” His mother looked at him disapprovingly. “Sorry,” he said, caving under her gaze.

She reached out and took the ring back to look at it again. “This was your grandmother’s. And she left it to me and said she wanted you to have it when you wanted to marry the right girl,” she explained with a smile.

Jake smiled back. “I didn’t know you had this. How come I didn’t know about it?”

Karen shrugged. “I didn’t want to freak you out. I didn’t know if you actually wanted to get married. And if you didn’t, I didn’t want you to think I wanted you to. If that makes sense. I wanted you to make your own choices for your own life. And if it went this way, I was going to give you the ring when you wanted it.” She handed it back to Jake and he held it in his palm, looking at the beautiful ring in awe. “Of course you’ll need to get it cleaned. And probably sized. Your grandmother had huge hands,” she added with a laugh. She looked at him staring at the ring. “She was adamant about how it had to be the right girl. And I can say without a doubt that I’m happy to have you give that ring to Amy.”

He looked up at his mother happily. “Yeah?”

“Oh yeah. That girl couldn’t be any better for you. Or for this family,” she responded, sitting down on her bed. “I liked her when I met her, but then she kept coming over when you were in witness protection and she just felt like family. I could tell she missed you as much as I did. It helped to have someone to share my pain with.”

Jake stared at his mom in confusion. He’d never heard that Amy visited his mom while he was gone. Why hadn’t either of these women mentioned it? What did they talk about? Did his mom make Amy her famous dishes from his childhood?

Jake shook his head, clearing out his thoughts. “I never knew that she came here while I was gone,” he said, asking for her to elaborate as he sat down next to her.

Karen nodded. “She did. The first time was maybe a week and a half after you left. She showed up at the door and apologized for dropping by, but she needed some sort of tie to you.” Jake could feel tears stinging his eyes as he pictured the two women he loved most bonding over his absence. His mother continued. “Soon we made it a fairly regular thing when she wasn’t caught up in a case. She’d come by and we’d talk and I’d cook her dinner.”

“What did you talk about?” Jake choked out.

Karen laughed. “Well, mainly you.” He nodded with a grin. That made sense. “But then we started finding other topics we could talk about. And slowly but surely, her visits weren’t such sad affairs but rather a nice distraction for both of us.” She patted his knee. “I mean don’t get me wrong, we were both devastated that you were gone.” He laughed with her.

“Wow. I didn’t realize,” he said in a hushed voice.

“Every time she came over at the beginning, I’d find her staring at your picture from the Academy. The one you called the blooper because you were laughing in the picture when you were supposed to look a bit more stoic.” He nodded in remembrance of the picture. His mother had framed it because she thought it was a better representation of her son. “After enough times of her staring sadly at it, I took it off the wall and gave it to her to keep.”

Jake looked at his mom in shock. “Really? But you always loved that picture.”

Karen nodded. “Yes and I still do, but I could tell she needed it more than I did.”

The two sat in silence as Jake absorbed all the new information his mother had just given him. He wondered why neither of them had mentioned any of this in the months he’d been back. Maybe they didn’t want to admit how hard it was for them while he was gone. He’d definitely noticed that with Amy. He’d talk about how hard it was to be in Florida and then she’d start to talk about what it was like back home. She’d get a certain amount of the way in and freeze, changing her story to make it seem less painful. He wanted to tell her that he could handle it, but at the same time, he didn’t know if he could handle it. He knew how exquisitely painful it was to be separated from Amy for months with no contact. He figured it would be a blow to hear in extreme detail how hard it was for her too.

His mother wrapped an arm around his shoulder as he sat there silently staring at the ring in his hand. “So you’re gonna tell me before you actually propose, right?”

Jake smiled at his mother and nodded. “You know I will.” He held up the ring and gestured with it. “And thank you for this.”

~~

Jake waited for Amy to leave the precinct to talk to witnesses before he gathered the gang in the briefing room. Rosa, Charles, Gina, Terry, and Holt were all in the room, staring at Jake, waiting for him to begin talking. He waited until it seemed like they were about to yell at him.

Jake spoke simply. “It’s game time.”

They all looked confused.

“Game time? What does that mean?” Terry asked.

“Oh, let me clarify,” Jake responded. He fished in his pocket and pulled out the ring, presenting it to them, Lion King style. “It’s game time!” He said grandly, gesturing to the ring. Gina gasped. Charles screamed. The other three just looked impressed.

Gina ran forward, inspecting the ring. “Where the hell did you get this?” She asked in awe.

“Yeah,” Rosa asked. “Weren’t you concerned about money?”

“Turns out my mom was holding onto my grandma’s ring for me,” Jake explained.

“Wait! This was Nana’s ring?” Gina asked exasperatedly.  Jake nodded. “I got her stupid apartment and Amy’s gonna get this dope ring? That doesn’t seem fair! She didn’t even know Nana!”

Terry stepped forward. “I think what Gina means is that we’re happy you got a ring.” Gina shook her head.

“I’m happy too,” Jake agreed. “It’s actually perfect because I think Amy would appreciate a family heirloom way more than some new jewelry store ring.”

“Oh you are so right, Jakey,” Charles concurred. “So is this the part where we help you plan your proposal?” he asked excitedly, rubbing his hands together.

“Actually, I already figured it out.” Charles looked visibly sadder. “But it’s going to involve all of you playing along,” he explained. “And of course, keeping it a secret until the actual time it happens.” They all nodded in agreement.

“So how are you going to do it?” Holt asked.

“I’m glad you asked, Captain,” Jake replied with a smile. “Do you all remember the lovely bet I had with Amy? To clarify, it was the bet I won.”

“We all knew what bet you were talking about,” Rosa retorted.

“Sure,” Jake answered. “Anyway, if you’ll recall, when I won said bet, I fake proposed to Amy. _This_ time, I’ll win the bet and I’ll propose to her for real,” he explained excitedly.

“What if you don’t win?” Gina asked.

“Wow, I’m hurt,” Jake replied. “Don’t worry, I’m gonna win.”

“But what if you don’t?” Holt asked.

Jake scrunched up his face. “And that’s where you, my lovely friends, come in.” They all stared down Jake. “If it gets close to the end and I’m losing, I’m gonna need you to throw me a bone. I’ll work a shift for you or you can throw me an easy arrest. Something to help me boost my numbers.” They all continued to stare at him. “Come on, Guys, you were all so willing to help out. Now you’re not going to?”

Charles piped up first. “Jake, you know I’ll help you!”

“Yes! Thank you, Boyle!”

Rosa shrugged, “I guess I can help you too.” Jake fist pumped the air. Everything was falling into place. There was just one piece left.

“Captain Holt, I need a favor from you,” Jake asked nervously.

“And what is that?”

Jake took a deep breath. “At the next morning briefing, I need you to make some comment about how our arrest numbers are down or something like that.”

Holt looked confused. “But your numbers aren’t down. They’ve been holding steady.”

Jake nodded quickly. “Yeah, I know, we’re great. I just need you to say it. Say they need to improve. Something! And then I’ll turn to Amy and jokingly say that we should make another bet since it improved numbers so much the last time. And given how crazy competitive Amy is, I’m pretty sure she’ll agree immediately.”

Holt nodded thoughtfully. “Do you think it’s smart to encourage such competition in your relationship right before you propose to spend the rest of your lives together?”

Jake stared at him blankly. “It’ll be fine.”

~~

It was the next morning and Jake was beyond nervous. He had three back up plans just in case this went wrong. They walked into the briefing and Jake plopped down next to Amy. His hands were starting to shake so he stuffed them in the pockets of his hoodie. He really hoped Amy couldn’t pick up on all of his nervous energy. She was turned around talking to Rosa about a case until Holt called their attention. Great. At least now her attention would be on Holt and not on how stupidly nervous her boyfriend was.

The moment came and Holt delivered. “Our arrest numbers could use some improvement. Any ideas, Detectives, on how we could do that?”

Jake was about to speak when Amy chuckled beside him. “Jake and I could always just make another bet. That really seemed to improve them last time.” Jake gaped at Amy. Were they _that_ in sync that she suggested it before he even could? She looked over at him and looked confused by his expression. “What? It was just a suggestion.”

Jake fixed his face. “I think it’s a great suggestion. I think we should do it! What are your terms, Santiago?” Amy looked thoughtful.

“Yeah, what will the terms be, Amy? You’ve already become one of the girls in Jake’s car,” Gina reminded her.

 Jake couldn’t take it. “You’re taking too long. If, no, _when_ I win, you’re gonna do all my paperwork for me for a month.”

Amy looked at him like he was crazy. “Fine. Give me more paperwork. You know I don’t hate it. But when _I_ win, _you’ll_ do all of my paperwork for a month. I know that’s truly torture for you, Jake.” Jake eyed her doubtfully.

“Well then,” Holt stated, “It seems we have a deal.”

Amy stuck her hand out for Jake. He grabbed it and shook it firmly. “It’s a deal.” She smirked deviously as she shook it back and echoed him.

Somehow this handshake felt like Jake was sealing his fate.

~~

**Notes for the Chapter:**

> I would love to hear your thoughts on this chapter!  
> This story has been fun for me to write which translates into quick updates.  
> Thanks for all the love so far!


	3. The Result

**Notes for the Chapter:**

> 1\. I'm sorry that it took me so long to get this chapter written. School just has a way of stopping me from doing things I enjoy.
> 
> 2\. I think this is the longest chapter I've ever written. Ever.
> 
> 3\. I have no idea how many arrests it is plausible to make in a certain amount of time so just bear with me. 
> 
> 4\. Thank you SO much for all the comments and kudos! :)

Day 1:

Peralta: 0, Santiago: 0

Everyone settled back at their desks after the meeting and Jake was giddy with anticipation. The key was trying to keep it under control so Amy didn’t suspect anything. That was going to be hard.

“So we didn’t set a timeline on this bet,” Amy stated as she rolled closer to her desk. She gazed at Jake with a challenging expression. “So what do you say? A year again?”

Jake panicked. A year? He couldn’t wait that long. “Umm…a year? Don’t you think that’s a little long? What about like two weeks?”

“Two weeks? A mere fortnight? Please, where’s the challenge? What’s wrong with a year? That’s how long it was the last time,” Amy replied.

Jake scrambled to think of possible reasons. “Uhh, I just think that the Captain wanted numbers up faster than that. Or whatever. How about a month?”

Amy shook her head. “How about six months?”

“How about a month?” Jake countered.

“You didn’t change your number. This is a compromise. I shortened my original number by six months.”

“Yes, and I lengthened mine two weeks. We’re good. How about a month?” Jake asked again.

Amy stared at him and he tried to keep his poker face up. After a beat she smirked and nodded her head slowly. She chuckled before saying, “I see what this is. You’re afraid of the long game. You’re afraid that if we set a long timeline, you won’t last. You’ll choke before the big finish.”

Gina laughed behind Amy. “Huh, sounds like she’s speaking from experience. Eh, Jake? Of course I am talking about –”

Jake looked around Amy to interrupt Gina. “We know what you’re talking about. Don’t be gross,” he said with a glare. He looked back at Amy about to reply to her before he felt the need to elaborate to Gina. Looking back at her he said, “Also, that is grossly inaccurate. I am great!” Looking at Amy pleadingly he said, “Amy would you please tell Gina how great I am?”

Amy looked uncomfortable. “Why?” All it took was an exasperated look from Jake for her to turn around to Gina and say, “I can confirm that what he’s saying is correct.”

Gina grinned deviously. “Yeah, that sounded real.”

“Whatever,” Jake basically yelled. “This has gotten massively off topic. I can handle the long game, Santiago. But you trying to stretch it out makes me think _you_ can’t handle the short game. Like you need a few months to really get going,” Jake challenged. He looked at Gina, “That was not me making a statement about anything.”

“You think I can’t handle a short challenge? Please! I can handle anything,” Amy nearly cried.

“I don’t know. I mean, you lost the last bet…” Jake said, leaning back in his chair with his arms behind his head.

Amy gasped softly, shaking her head at him. “Fine. Have it your way then. Three months.”

Jake sat up and narrowed his eyes at her. “Two.”

Amy huffed, “Fine, two,” she conceded, reaching across to shake his hand. “But that’s not even a real challenge.”

Jake shrugged cockily, “Prove it.”

~~

Day 3:

Peralta: 0, Santiago: 1

“Oh my God! Really? Thank you!” Amy’s hand almost shook as she put her phone back. She sat there silently for a second before standing abruptly. She cleared her throat quickly. “Uh, Detective Peralta? Could I speak with you for a minute?” She asked overly formal.

Jake looked up at her curiously. “Sure…”

Her eyes went big and she nodded away from the bullpen. “Privately?”

“Ahh,” Jake said, showing his understanding. “Of course,” he answered, standing up and motioning for her to lead the way.

She led him into an interrogation room. He looked around questioningly. She followed his glance. “No one was using it,” she explained.

He nodded. “What’s up?”

She grabbed his arms and squeezed. “We got it!”

He looked confused. “Got what?”

“Remember that apartment I showed you like two weeks ago? That we then applied for?” She asked, trying to trigger his memory.

Understanding spread across his face. “Ohhhh! Right,” he said with a nod. Suddenly his eyes when big and he gripped her arms too. “Wait, we got it?” She nodded excitedly. “Amy, that’s awesome!”

“I know!” She took a deep breath. “There is a slight catch.” Jake looked at her skeptically. “We have to move in by the 20th or else it goes to another couple.”

“That’s a weird stipulation,” Jake argued. She could see when it dawned on him. “Wait, the 20th is just over a week from today.”

“Yep eight days. That does cause a bit of a challenge. But we’ve done crazier things than this. Right?” Amy asked, hoping he was still on board.

Jake nodded thoughtfully. After a long pause, Jake answered, “We’re going to need some backup.”

~~

Day 11:

Peralta: 2 Santiago: 1

Somehow they’d roped the squad into helping them move. Even Holt had volunteered his service even though Amy and Jake had felt too awkward to ask him. Admittedly, Terry had been doing most of the work, though they had told him they were using him for his ridiculous muscles.

Amy was yelling at Hitchcock about not touching the breakables when Jake spotted Rosa going out for another load from the truck. He quickly ran after her, noting that everyone else seemed to be absorbed with a task inside the apartment.

“Hey, need a hand with that?” Jake asked, trying to be friendly. Rosa turned around and looked at him.

“It’s a lamp,” she replied blankly.

Jake stepped closer to her. “Okay, I need a favor from you.”

Rosa stared at him. “Aren’t I in the middle of a favor for you, Jake?”

Jake nodded. “I need one related to the bet.” Jake paused, waiting to see how she’d react. As per usual, no reaction. “You know, since if I don’t win I don’t get to propose to Amy.”

Rosa rolled her eyes. “Just say what you need.”

Jake fist pumped the air. “Great. I noticed you’re working next Saturday. I would like to take that shift. I need to do some serious damage on this bet. Amy and I have barely made any arrests in the last week because we’ve been so focused on moving in time. So now that we’re moved in, I need to really get things going.”

Rosa shrugged. “Fine.” After a pause she added, “Wait, you’re about to start living with Amy. Don’t you think she’ll notice if you aren’t there?”

Jake grimaced. “Yeahh, that’s the other part of the favor. I need you to distract her.”

She glared in return. “What? Come on, Peralta.”

“Look, I know spending time with other people outside of work is your idea of torture, but you’re right, Amy will know where I am,” Jake pleaded.

“And what do you suppose we do?”

“You could…ooh, go shopping. I liked your apartment that one time you let us see it. You could tell Amy that you guys could go shopping for new decorations or something,” Jake answered.

“So I’d really be doing you _two_ favors. One, distracting Amy. And two, getting her to not put up her grandma decorations. You’re asking a lot of me.”

“I know I am. I’m sorry. I just – I have this plan in my head and if something goes wrong, I –”

“Stop crying. I’ll do it,” Rosa stated. “But when this bet is over and done with, you’ll owe me one.”

Jake nodded vehemently. “Deal. Seriously.”

“Hey! What are you two lazy bones doing down there? We have jobs up here that need to be done!” Amy yelled out the window.

Jake and Rosa grabbed things from the truck and headed inside. “So that’s who you’re gonna spend your life with, huh?” Rosa goaded.

“Shut up.”

~~

Day 18:

~~Peralta: 2, Santiago: 3~~

Peralta: 4, Santiago: 3

It was Jake’s lucky day, it seemed. He’d been working for two hours and he’d already booked two criminals. Lucky for him they’d been working together. It had been an easy arrest that had easily doubled his numbers. Amy would be livid when she saw that he was once again in the lead. But either way, he was in a giddy mood as he sat at his desk doing the paperwork for two different arrests.

He didn’t even notice the goings on around him until the Captain sat down next to his desk. Jake looked up at his superior with a surprised expression. “Captain, what are you doing here?”

“I’m picking up something I forgot here yesterday. I think the better question is, what are _you_ doing here, Jacob?”

Jake shrugged. “Covering for Rosa. She wanted to have some wild weekend or something. I don’t know.”

“Really? Then why did my husband just run into Diaz and Santiago at a coffee shop not twenty minutes ago?” Holt inquired, cornering Jake.

Jake was flustered. “Rosa goes crazy over her java, man.”

“Really? What _I_ think happened is that _you_ took this shift from Diaz so that you could gain headway on the bet. And Diaz was tasked with distracting Santiago so that she wouldn’t notice your absence from your newly established home while you snuck here for the day to try and top her.” Holt held a steady stare on Jake. “Tell me, Peralta, which part of that is wrong?”

“Well, Sir, you failed to include the part where I arrested two criminals this morning,” Jake answered confidently.

Holt stood up, poised to leave. “Listen, I know that winning this bet is important for you. Given the reasons you have for doing it, I am fine with you doing all this again. But maybe let Diaz work her shifts and you work yours. Skulking around the precinct will not help anything. Deceit is not a good game to play, Jacob.”

Jake nodded slowly. “On the other hand though, does it really matter who does the work as long as it gets done? Like does it matter that I arrested someone that Rosa could have arrested if I hadn’t begged her for her shift? As long as the bad guys get caught that’s all that matters, right?” Holt stared back at Jake blankly. “I read you loud and clear, Captain.”

After Holt left, Jake leaned back in his chair, trying to recapture the victory he was feeling before getting chastised by his superior. He reached for his phone in his pocket. As he pulled it out, he noticed that it wasn’t locked. In fact, it was in the process of calling Amy.

“Holy crap!” Jake yelled, stabbing at his phone with his finger to hang it up. Once he’d hung up, he mentally scrambled back through his conversation with Holt. If Amy heard, she’d definitely know he was at work. But he was also trying to see if Amy would know that his plan was to propose. He didn’t think either of them had straight up said it. But freaking out would be an understatement. Maybe Holt was right and he shouldn’t sneak into work anymore.

~~

Everything seemed off to Amy. First, Jake had gotten out of bed before she did. That never happened. Even on work days she felt like she had to roll him out of bed. Second, he was dressed. That should have been a red flag for her. Jake never wore real clothes on a Saturday before noon unless they had somewhere to be. As far as Amy knew, they didn’t have any plans for the day. Third, and by far the weirdest thing, was Rosa showing up at their apartment and asking Amy if she wanted to go shopping. Yes, she and Rosa were in the minority of women around the precinct. But it wasn’t like they embraced that and did girly things together. They drank together _a lot_ , but never in the history of knowing Rosa had they ever been shopping.

“Why do you want to go shopping with me?” Amy asked bluntly.

“I just moved into a new apartment and I wanted some new stuff for it. I figured since you guys did too, maybe you’d want to do the same,” Rosa replied. She still wasn’t convincing Amy that something wasn’t off.

Amy stared at her for a long beat. “But why me? It’s not like you’ll ever ask me to your apartment. Or like you’d really care what we have in our apartment.”

Rosa motioned for Amy to step closer. “Look, I know the old lady scene was working for you. And I know the 12 year old scene was working for Jake. But I figured maybe since you lived together, you could actually have things around your place that look like a couple in love living together and not a pre-teen living with his grandma.”

Amy gaped at Rosa. She had many defenses rattling around in her head but she couldn’t get any out before Rosa continued. “Just come with me. What else are you going to do? Clean? Sit on the couch and watch TV with Jake all day? Gross.”

Amy shook her head. “Whatever. Just give me a minute to change.” Without a doubt Amy Santiago was in for the weirdest day of her life.

They had been out for a few hours, browsing different shops. Amy had actually picked up some nice pieces that she thought would fit their place well. It had been pretty awkward though. Amy had known Rosa for a long time, but she’d never really gotten Rosa to open up. Well, at least not sober. There were a lot of long stretches of silence between them. They would talk about work but that only went so far.

Finally Amy plucked up the courage to actually ask Rosa about her life. “So, um, have you heard from Adrian at all?” She asked hesitantly.

Rosa looked at Amy before turning back to the vases in front of them. “No.” Amy wanted to press for more information but she really figured that was all she’d get. To her surprise, Rosa continued. “I’ve reached out a lot. It’s hard to reach out to a ghost though. My guess is he thinks that my messages saying that Figgis is in prison is just Figgis trying to lure him out of hiding. So I haven’t heard from him.”

Amy was shocked that she’d gotten that much out of Rosa. She reached out and touched her shoulder. “I’m so sorry, Rosa.” Rosa shrugged it off. “Have you tried finding him?”

“He’s a ghost right now. It would be pretty impossible to find him. Maybe someday he’ll realize Figgis is gone and come back. I’m okay though.”

“Really?”

Rosa nodded. “Yeah. I always am.” Amy looked unsure. “But thanks for asking. Really.”

They were browsing the curtains when Amy felt her phone vibrate. She reached in her pocket and saw that Jake was calling. As she answered she heard a conversation already happening. He must have butt dialed her. She could hear him talking with Holt.

“ _You snuck here for the day to try and top her. Tell me, Peralta, which part of that is wrong_?”

“ _Well, Sir, you failed to include the part where I arrested two criminals this morning_.” Amy gasped softly. He was at work?

“ _Listen, I know that winning this bet is important for you. Given the reasons you have for doing it, I am fine with you doing all this again. But maybe let Diaz work her shifts and you work yours. Skulking around the precinct will not help anything. Deceit is not a good game to play, Jacob_.” Hearing Rosa’s name she remembered that Rosa had been scheduled to work. She looked up at her companion who was weighing the merits of the green drapes in front of them.

“ _On the other hand though, does it really matter who does the work as long as it gets done? Like does it matter that I arrested someone that Rosa could have arrested if I hadn’t begged her for her shift? As long as the bad guys get caught that’s all that matters, right? I read you loud and clear, Captain_.”

Amy held her phone in her hand, not hanging up in her confusion. She stared at Rosa. Looking back down at her phone, she saw that Jake had hung up. Shaking her head, she focused back on Rosa. “So, remind me, why did you want to go shopping with me again?” Amy asked suspiciously.

Rosa looked over at her with a confused glance. “What?”

Amy continued. “Because if I recall, you were supposed to work today, right?” Rosa kept looking at Amy. “But as I just found out, Jake is at work. And according to him, he’s covering your shift.”

“He told you that?” Rosa asked.

“No he butt dialed me and I heard him tell Holt that.” Rosa nodded. Amy reached out and smacked her arm. “Come on, Rosa! Remember when we established that as the women in the office we needed to stick together? But you’re here helping Jake advance on the bet? This hurts.”

“I’m sorry. He cornered me and begged me. You’ve seen his puppy dog face. Even for me, it can be hard to say no to.”

Amy shook her head disgustedly. “I’m gonna remember this, _Diaz_.”

Rosa stared at her blankly. “Really? You’re going with last names?”

“Yeah, so that you know how betrayed I feel. You’re lucky I’m not just calling you Detective.”

They made their purchases and headed home. Amy wasn’t really that mad at Rosa. She knew full well how persuasive Jake can be when he really wants to be.

She redecorated as she waited for Jake to return from the precinct. In the end, Amy never really acknowledged that Jake had gone to work. She knew he had to be waiting for it. Instead, she plotted.

~~

Day 30:

Peralta: 9, Santiago: 10

It hadn’t been a full two weeks since Rosa had distracted Amy from Jake’s betrayal, but Amy and Jake had been cracking down on work. They’d both been working crazy long hours. Luckily for both of them, they’d both made plenty of arrests. Amy was currently up by one, but it wasn’t enough.

She waited till Jake left the bullpen to walk over to Charles’s desk. “Hey Charles! How’s it going?”

Charles looked up happily from his paperwork. “Good. How about you? How is it living with Jake? Are you two just totally blissed out? Tell me everything.”

Amy scrunched her nose in mild disgust. Charles was always so invested in their relationship. It was sweet, but also sometimes invasive. “Yep, it’s actually been really nice.” She thought to herself about how they hadn’t really been at home too much because they’d been working their asses off. But she didn’t feel the need to mention it to Boyle. She leaned closer to him. “You know, I can’t help but notice that you and Jake haven’t gotten to spend much time together lately. I’ve always thought your friendship was so special.” Maybe she was laying it on a bit thick, but she didn’t care.

Charles looked thoughtful. “Yeah. I just love Jake. And you’re right, it’s been a while since we had a guys’ day. What with my family and you two moving in together, it’s left little time for our Jake and Charles time.”

Amy reached out and patted his arm. He was playing right into her trap. “Well why don’t you do something this Saturday?”

Charles perked up quickly. “Oh that would be great! Yeah!” After a second, he looked glum. “Wait, I can’t. I work this Saturday.”

Amy shrugged, hoping to seem nonchalant, “Well, I could work that for you. I mean, I know it would mean a lot to Jake too. He mentioned the other night that he misses just hanging with you.”

Charles’s eyes grew. “Really?”

Amy nodded, a smile gracing her face. “Sure.”

“Wow. Thank you so much Amy. This is going to be so much fun! I’m gonna go find Jake and tell him!” Charles exclaimed, getting out of his seat.

Amy stopped him. “Hey, just tell him that you should do something. Don’t mention work. He’d feel bad if he knew you were missing a shift to spend time with him.”

Charles nodded thoughtfully. “You’re right. Jake is such a great guy.”

Amy smirked. “Isn’t he?” She agreed with a laugh.

Charles went to find Jake and Amy walked back to her desk. She saw Gina smiling at her and nodding as she sat down in her chair. “What?” Amy asked.

“It’s always the quiet ones,” Gina said in awe.

“I’m not really that quiet,” Amy replied, confused.

“Fine. It’s always the ones you least expect,” Gina corrected.

“What do you mean?” Amy asked, still confused by Gina’s comments.

“The ones who end up being the most manipulative. You just played Charles like a freaking fiddle. And I guarantee you he has no idea,” Gina clarified. She beamed at Amy. “I am actually proud of you right now, Amy Santiago. So damn proud.”

Amy scooted her chair closer to Gina’s desk. “Please don’t tell them. I need to work his shift.”

Gina waved her hand and scoffed. “Oh please. I want to see how this turns out.” Amy thanked her. But Gina kept going. “So who do you think we can manipulate next?” Amy rolled her eyes and rolled back to her desk.

~~

Day 32:

Peralta: 10, Santiago: 13 (unbeknownst to Peralta)

Jake and Charles were having a great time together. Charles had been right, it had been a while since they’d hung out just them. Somehow, Jake had even convinced Charles to let him pick the restaurant they went to for lunch. Jake was relieved when he didn’t have to eat some animal’s stomach or something.

Charles of course had a billion questions about living with Amy. He liked to remind Jake every so often that he was the one who realized Jake’s feelings for Amy first.

“So are you nervous?” Charles asked.

“Nervous? About what?”

“About proposing to Amy. She’s the love of your life. Aren’t you at least somewhat nervous? I mean what if she says no?”

Jake stared at his friend. “Why would she say no? We live together. We survived months away from each other while I was in Witness Protection. What reason does she have to say no?” Jake asked. Before Boyle could reply, he jumped back in. “And no, that was not me asking you to give me reasons.” Jake sat there thinking. “The only thing I’m really nervous about is winning this damn bet. I don’t have another plan in place.”

Charles looked at Jake thoughtfully. “There’s no reason that you can’t still propose to her if she wins. You could say, “Amy I’m so proud of you for winning this, be my wife.” It doesn’t just have to be because you won.”

Jake thought it over. He started shaking his head. “Nope. The whole reason to do the bet was because I fake proposed to her last time. I _have_ to win,” Jake explained with a sigh.

“You still have almost a month left. You’ll do it, Buddy,” Charles reassured him.

Jake nodded at his friend. “Thanks.”

They were leaving the restaurant when Charles reached for his wrist. “You know, we’re pretty close to the precinct. Do you mind if we stop by there? I forgot my watch there yesterday.” Jake shrugged and agreed.

They walked into the precinct and Jake sat down at his desk as Charles ran to his locker to get his watch. Jake looked over at Amy’s empty desk. That was when he saw it. A blazer draped across the back of the chair. He stood up and walked over to Amy’s desk. He gasped at the sight of it. The computer was on and logged in. There was a still steaming mug of coffee sitting there waiting to be consumed. He opened her bottom drawer and saw her purse. “That liar,” he gasped to himself.

He went back to find Boyle but he was not in the locker room. So he decided to search for him. He walked past the janitor’s closet and heard voices. He leaned closer to the door so he could hear them. He distinctly heard the voices of his best friend and his girlfriend.

“But Charles, you are not supposed to be here,” Amy cried.

“I told you I just came back to find my watch. If you just stay in here, Jake will never know you’re working,” Boyle responded. Jake was aghast. Had they been plotting behind his back? Is that why Boyle suggested Jake could propose either way the bet won out.

“Okay. Please just go. And text me when you’ve left the building so I know I can leave this closet. I really don’t want Jake to know I’m here,” Amy pleaded.

Jake considered his options. He could open the door and scare them both or he could stand there and wait for them to open the door themselves. They started to open the door before he could make up his mind. Quickly he crossed his arms and adopted a questioning expression. They both jumped at the sight of him. “Oh why if it isn’t my best friend and my girlfriend hiding in a closet together…”

Amy stepped forward. “Jake it isn’t what you think.”

“Oh okay. So you didn’t get my best friend to distract me all day so you could work and add to your numbers for the bet?” Jake asked confidently.

Amy opened and closed her mouth. “Oh, um, so it’s exactly what you think,” she conceded.

Jake narrowed his eyes at them and nodded.

Charles leapt forward. “Jake, she told me she’d work for me so we could spend time together.”

Jake looked at Amy. “Oh? So this was all your idea then?”

Amy straightened up. “Yes, just like how it was all _your_ idea to have Rosa distract me with shopping.”

Jake recoiled. “Wait, you knew about that?”

Amy glared at him. “Of course I knew about that, Jake, you butt dialed me for crying out loud!”

He grimaced in response. “You never acknowledged it.”

Amy motioned to the three of them. “Consider this me acknowledging it.”

Jake looked back and forth between them. “Well I think I’m going to go home. I’ve had a bit too much betrayal for today.” He could see Charles starting to chase after him as he turned to leave. 

He could hear Amy yell to him, “It’s not betrayal if it’s revenge!” On his way to the elevator, he noticed the board with the current standings. He nearly clutched at his heart to see how much she’d done.

~~

Day 58:

Peralta: 24, Santiago: 25

They laid on the couch, both not having the energy to move. They’d worked for so many hours that Jake honestly couldn’t remember the last time they’d both been at the apartment. Getting through the last days of the bet was hard. Every time one of them tied it up, the other scrambled to find another arrest. It was a vicious cycle that had led them to work for close to 48 hours. They’d taken short breaks to eat. Once Amy had insisted Jake shower so he gave himself an hour before he was back at it.

They were nearly falling asleep at their desks when Captain Holt had insisted they go home.

“We’re fine, Captain,” Amy had insisted, stifling a yawn.

“Yeah! Look at us. Top of our game,” Jake agreed as his head lolled off his hand and hit his desk.

The captain looked unimpressed with both of them. “Go home. You’re of no use to us half dead.”

So they’d trudged home, getting food on the way there because the food in the apartment was far past edible. They’d eaten and were laying on the couch, unable to move.

“I think this bet is slowly killing us,” Amy said barely above a whisper.

“I don’t remember it being this crazy last time,” Jake agreed.

“Maybe it’s because it was over a whole year, not condensed into two months,” she argued.

“Nah, that’s not it,” Jake countered. He looked over at Amy. “At least when I win this time you’ll actually want to go on a date with me.”

She chuckled and reached out to grab his hand. “I don’t know. I think you’re underestimating how mad I’ll be if I lose again.” For a second Jake panicked, but then she laughed and squeezed his hand. He squeezed hers back.

They sat there in silence. Jake was remembering the last week of the last bet. And then of course the whole night after winning it. Sitting up on that rooftop with Amy was still a great memory for him. He smirked to himself. “Can I confess something to you?” She turned to look at him and nodded. “That awful date we went on? That was the first time I realized that maybe you weren’t totally disgusting.”

Amy sat up and turned her whole body toward him. “Excuse me?”

Jake laughed and looked at her. “I don’t know what it was but it was when I started to realize I had feelings for you.” She looked like she was evaluating him. She smiled at him and curled up next to him. “We’ve always made a good team,” Jake mused.

He felt Amy nod against him. “Yeah, way better than that relief team would have been.”

Jake turned his head to try and look at her. She looked up at him. “You knew about that?” He asked.

She giggled and nodded. “Yeah, Holt thanked me the next morning for turning down the relief team. I don’t think he knew it was news to me. I walked out of his office thinking pretty highly of you, Jake Peralta. Until of course minutes later when that stripper showed up.”

Jake laughed. “Don’t worry; I have no stripper plans in the works. Unless of course you want _me_ to…” Amy died laughing, her body shaking against his. Jake wrapped an arm around her. “You know, I’m a little offended that when I offered to strip for you, your answer was laughing.”

Amy struggled to stop laughing. “My bad, Babe, my bad.” She cuddled closer into Jake’s side, sneaking a leg between his. He could feel her breathing steady out. It wasn’t too long before she was asleep against him and not too long before he joined her.

~~

Day 60:

Peralta: 25, Santiago: 25

They were waiting for the elevator. Jake felt in his bag for the hundredth time to make sure he had his grandmother’s ring. Today at 6:00, provided Jake didn’t choke, he was going to propose to Amy. It was an insane feeling. She turned to him before they stepped on the elevator.

“Okay, you know we’re both terrible losers,” Amy pointed out. Jake nodded in agreement. “So I think it would be best if we left Jake and Amy, loving couple, behind in the elevator. It could get brutal today. How does that sound?”

Jake stepped on the elevator. “I think that sounds smart. Who knows what will be said today? I apologize in advance if I say something in the heat of the moment that I will eventually regret.”

“Mmhmm, same here,” Amy agreed.

They held hands as they rode up to their floor. At the third floor, they let go of each other. Jake pulled her in for a quick kiss. She smirked at him before the doors opened. They looked out at the bullpen. Jake looked back at her.

“Detective Santiago,” he greeted.

She nodded back, “Detective Peralta.”

They stepped out of the elevator and walked to their desks, both ready to get in as many arrests in one day as possible.

Somehow they both got one in before lunch. Jake didn’t even take the time to gloat. He immediately started on another case.

It was around 5:00 when Rosa started heading for the elevator. Jake ran and jumped in her path. “Where ya going, Rosa?”

Rosa glared at him. “I’m going to make an arrest.”

Jake’s eyes went big. “Rosa please let me have it. We’re tied. There’s an hour left. Please.”

“Jake, I can’t just _give_ you my case. I’m sorry,” Rosa said, stepping around him.

Jake stood there staring after Rosa, feeling betrayed beyond belief. He heard someone walk up to him and he turned to see Sarge standing next to him.

“You didn’t hear this from me, but there’s a burglary in process at the jewelry store down the street,” Sarge whispered.

“Are you serious?” Jake asked with a giddy tone.

“If you go now, you could catch him with his loot,” Sarge offered.

Jake didn’t even wait for more information before he ran from the bullpen.

Sure enough, Sarge was right. He caught the guy on his way out of the store with $2000 worth of watches. Jake sat with him in the patrol car for 30 minutes. He wanted to plan it _just_ right when he strolled in and won the bet.

~~

Amy walked back to her desk and sat down. Looking at the board, she noted they were still tied. She looked across to Jake’s desk but he wasn’t there. She turned and looked around the bullpen, but he was nowhere to be seen. She checked her watch and it was 5:53. She ran into the break room but he wasn’t there. She ran into an interrogation room but he wasn’t there either. She checked the briefing room and the bathroom but he was nowhere to be seen.

Frantically she asked, “Has anyone seen Jake?”

Everyone looked up and shook their heads.

Finally Charles said, “I think he might be out on a case.”

“What?” Amy practically screamed. Sure enough, the elevator doors opened and in walked Jake, holding onto a perp.

~~

“Dude, you arrested me like an hour ago? Why are we just sitting here?” The perp asked from the back seat.

Jake turned to look at him. “One, it wasn’t an hour ago. If anything it was like twenty minutes. And two, you are part of something bigger than yourself. You, sir, are giving me quite possibly the greatest gift in the world.” Jake smiled to himself. “So no more questions, okay?”

Jake timed it perfectly. It was 5:55 when he walked into the precinct, perp in stride. Amy looked like she was a mixture and dumbfounded and pissed off. He hoped more dumbfounded. On his way to the holding cell, he tipped his head to the sergeant, his quiet way of thanking him.

Jake quickly strode to the board in front of Gina’s desk and updated his number. “Five minutes left,” he announced.

“No,” Amy yelled. “No! This isn’t fair. Not again!” Jake stared at her.

“Amy, you have five minutes, can’t you make an arrest in that time?” Gina goaded.

Amy glared at her. Then she turned her glare on Jake. “How did you do this? Did you have _all_ of them helping you?”

Jake just stared at her. She threw a file back on her desk angrily, tipping over a pile, causing a huge mess. She stormed past Jake and out of the room, muttering under her breath. So she was definitely more pissed off than dumbfounded. He wasn’t sure he’d ever seen her that angry. He wanted to follow her but he didn’t know what he would even say. After all, they had agreed to leave their loving couple status at home for the day. Jake wandered away from the bullpen. He didn’t want everyone’s eyes on him.

He found himself in the briefing room, questioning every decision he’d made since he’d returned from Florida. He’d been so sure the bet was a great idea. Amy had certainly been enthusiastic about it. But seeing her reaction left him second guessing it all. Maybe today wasn’t the day to propose after all.

Charles ran into the briefing room followed by Gina, Rosa, and Sarge. “Jake, what are you doing in here? You have two minutes left!”

Jake looked at them all. “Yeah, I’m not doing it.”

They all gaped at him. “What? But that was the whole point of the bet,” Sarge reminded him.

“Guys, did you just see that?” Jake asked, pointing to the bullpen, reminding them of Amy’s outburst. “I don’t want to propose to her like that. While she’s that angry. God, what if she says no because she’s pissed at me?”

“She’s not gonna say no,” Rosa insisted.

“You don’t know that, Rosa,” Jake replied.

“Come on, Jake, you have to do this,” Gina pressed.

Jake shook his head. “No, actually I don’t. I wanted it to be perfect. I guess I can find another time. The Captain was right after all. This competition wasn’t smart.”

They all overlapped in their efforts to convince him to go through with his plan. He heard the Captain’s voice from the back of the room. “I think you should do it, Peralta.” They all turned to look at him.

“Really?” Jake asked quietly.

“I’ve had a long career,” Holt explained, “And let me tell you this, making arrests is a great feeling. But at the end of the day, or at the end of your career, it doesn’t matter the number of arrests you have. It matters who you have to go home to.”

Jake stared at Holt, letting what he said sink in. He slowly started nodding. He turned to the rest of the squad. “Okay, I’m doing this.” They all cheered. “Charles, I gave you the ring, right?” Charles nodded. “And you know when the hand off is?” He nodded again. Jake turned back to Holt, “Thank you, Sir.” Holt nodded too.

“Jake, you have like, 30 seconds,” Rosa informed him. Jake started walking back toward his desk. One by one he saw the others leave the briefing room and get in position. Amy was sitting at her desk. She looked up when Jake approached.

“What? Come to gloat?” She asked, defeated. The urge to call it off came back to him. He looked back at the squad. Sarge nodded at him, encouraging him to continue.

Jake pulled on his cockiest voice. “Yep. You know that’s what I do best.” He grabbed Amy’s hand and positioned her by his desk. “Let’s see, I think you were right about… _here_.” Amy looked confused. He looked down at his watch. “Aaaand, seven…six…five…four…three…two…one! That’s it! Jake wins!” He pulled the boom box out the same way he had the last time. He hit play and Celebration started playing.

“Really? The same song?” Amy whined.

Jake just smiled as the squad set off their confetti cannons and he danced around them. He danced past Boyle who sneakily passed him the ring box. The rest of the squad was dancing but Amy looked unimpressed. He danced toward her, nervous as hell.

He danced right in front of her before dropping down on one knee. Instantly her face changed from aversion to awe. He presented the ring box and opened it. She covered her mouth as she looked from him to the ring and back to him. “Amy Santiago, you have made me the happiest man on Earth,” he felt choked up. He swallowed past the lump in his throat. “Will you marry me?” He asked, unable to contain his giant smile.

She had tears in her eyes. She gaped at him. “Is this for real?”

Jake nodded enthusiastically. “100 percent.”

She smiled to match his. She started nodding happily. “Yes! Of course, yes!” she exclaimed through the tears rolling down her face.

Jake quickly slid the ring on her finger before jumping up to kiss her. He pulled her to him and kissed her passionately. She wrapped her arms around him and pulled him even closer. Neither of them cared that the rest of the squad was watching. Slowly they pulled away. Jake rested his forehead against Amy’s and stared in her eyes for a beat. Slowly they untangled themselves from the other and Jake grabbed her hand and raised it. “She said yes!”

Everyone cheered again, setting off another round of confetti cannons. When Jake could finally pull his attention from Amy, he noted that Charles seemed to be crying too. Everyone was happy for them. Even Rosa and Holt were smiling. Jake looked back at Amy and she was staring at him with nothing but love in her eyes. Jake leaned back in and kissed her again.

The Captain cleared his throat, “Squad, to the briefing room.” Everyone including Jake and Amy started to move toward the briefing room. Holt looked back at them and shook his head. He was giving them a moment to themselves.

They kissed again. After they parted Amy said, “I love you so much, Jake Peralta.” Jake leaned in and kissed her quickly again.

“I love you too.” He kept staring at her, trying to decide if he should tell her the full story. “I almost didn’t do it,” he admitted.

“Why?”

“Because I felt bad that you were so upset.”

Amy reached up and touched his cheek. “I’m sorry. I had no idea you were planning this. I was…sort of planning something of my own for when I won.” Jake looked confused. “I was…gonna to propose to you when I won.”

Jake laughed. “Really? I did this whole bet so that I could propose to you.”

“But I suggested the bet,” Amy reminded him.

“Yeah, we are weirdly in sync because I was actually going to suggest it but you beat me to it. Holt only brought up the numbers thing because I asked him to…” Jake informed her.

She shook her head in awe. Suddenly it looked like something dawned on her. “Oh my god! No wonder you didn’t want to make the bet go for a year!”

Jake nodded happily. He didn’t think he’d ever been happier than in this moment. Not when he graduated from the Academy. Not when he got bumped to Detective. Not when he solved a ridiculously hard case. Not when he and Amy finally got together. Not when he got back from Florida. No, _this_ was the pinnacle of his happiness. Knowing that he would spend the rest of his life with the woman in his arms was the best feeling in the world. Period.

Slowly the squad walked back into the bullpen, signaling that it was time to get back to work. They all sat back down at their desks. Jake couldn’t help but notice that Amy couldn’t stop staring at the ring on her finger. She smiled at him when she caught him looking at her. Behind her, Holt walked out of his office.

“Attention everyone! At the end of shift, there will be a party at Shaw’s Bar to celebrate our newly engaged friends.” Then he simply turned back and walked into his office.

Amy looked at Jake. “Did you plan this too?”

Jake shook his head. “No.” He looked around to see the squad sharing knowing looks. “I think this was all them.”

~~

At the end of shift, they all started migrating toward the elevators. Amy was tucked into Jake’s side as they waited for the elevator. Charles stood in front of them. He looked at them expectantly. “So, Jake, I have to wonder how long I’ll have to wait before you ask me to be your best man. As you know, I’ve already written my speech.” Jake shook his head amusedly. At the ding, Charles turned around to get on the elevator, but he didn’t stop talking. “Also, guys, I have some great ideas for your wedding…”

Amy flashed Jake a look of horror. Jake just shook his head. “And so it begins.”  

**Notes for the Chapter:**

> Thank you so much for all this support on this fic! For my first time writing for this show, it's been a great reception. I have a bunch more ideas brewing so we'll see when I find the time to write them. 
> 
> Please let me know what you thought of this chapter! I love hearing from y'all! :)

**Author's Note:**

> This is my first time writing for this fandom. EEk! So I'd really love to hear how it was! 
> 
> I love this show and its characters so much! 
> 
> I'll likely put this one out pretty quickly because I'm anxious to finish writing it.
> 
> I'm three-drink-amy on tumblr. Feel free to come chat with me!


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